Synthesis of 4(3H)quinazolinimines with selective cytotoxic effect on human acute promyelocytic leukemia cells

Becerra, Alexandra; Quintero, Celso; Morales, Valeria Rodríguez; Valderrama, Mauricio; Aguirre, Adam; Faúndez, Mario; Rojas, René S.

doi:10.1016/j.bmc.2016.07.007

Cited by 8 publications

(5 citation statements)

References 32 publications

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“…In one manifestation, the use of a 2 H‐labelled substrate allows the SABRE effect to be successfully focussed into the protons of a second substrate 22, 23. It has also proven possible to stabilise the active SABRE catalyst in order to successfully hyperpolarise weakly interacting substrates when substoichiometric amounts are available 7, 24, 25. Specifically, we show here that complex 2a of Scheme 1 readily forms through the binding of two indazole ligands and one acetonitrile ligand.…”

Section: Introductionmentioning

confidence: 83%

Harnessing polarisation transfer to indazole and imidazole through signal amplification by reversible exchange to improve their NMR detectability

Fekete

Rayner

Green

et al. 2017

Magnetic Reson in Chemistry

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The signal amplification by reversible exchange (SABRE) approach has been used to hyperpolarise the substrates indazole and imidazole in the presence of the co‐ligand acetonitrile through the action of the precataysts [IrCl(COD)(IMes)] and [IrCl(COD)(SIMes)]. 2H‐labelled forms of these catalysts were also examined. Our comparison of the two precatalysts [IrCl(COD)(IMes)] and [IrCl(COD)(SIMes)], coupled with 2H labelling of the N‐heterocyclic carbene and associated relaxation and polarisation field variation studies, demonstrates the critical and collective role these parameters play in controlling the efficiency of signal amplification by reversible exchange. Ultimately, with imidazole, a 700‐fold1H signal gain per proton is produced at 400 MHz, whilst for indazole, a 90‐fold increase per proton is achieved. The co‐ligand acetonitrile proved to optimally exhibit a 190‐fold signal gain per proton in these measurements, with the associated studies revealing the importance the substrate plays in controlling this value. Copyright © 2017 The Authors. Magnetic Resonance in Chemistry published by John Wiley & Sons Ltd.

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Section: Introductionmentioning

confidence: 83%

Harnessing polarisation transfer to indazole and imidazole through signal amplification by reversible exchange to improve their NMR detectability

Fekete

Rayner

Green

et al. 2017

Magnetic Reson in Chemistry

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“…Quinazolin-4(3 H )-imines represent a privileged class of annulated six-membered aza-heterocycles with diverse biological activities such as antimicrobial, antihypertensive, antiproliferative, cholinesterase, and cMET kinase inhibitory properties . Furthermore, these molecules could serve as precursors for quinazolin-4(3 H )-one derivatives .…”

mentioning

confidence: 99%

Synthesis of Substituted Quinazolin-4(3H)-imines From Aryldiazonium Salts, Nitriles and 2-Cyanoanilines via A Metal-Free Tandem Approach

et al. 2017

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A transition metal-free synthesis of multisubstituted quinazolin-4(3H)-imines has been realized by the direct reaction of aryldiazonium salts, nitriles, and 2-cyanoanilines in a one-pot fashion. This strategy utilizes the in situ formation of reactive N-arylnitrilium intermediate, which undergoes further tandem cyclization with consecutive formation of N-C bonds. Broad functional group compatibility, mild conditions, shorter time, and operational simplicity are the notable features of this report.

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“…Quinazolin-4(3 H )-imines (QIs) are nitrogen heterocycles with interesting biological properties. Derivatives containing this core have shown activity as acetyl and butyrylcholinesterase inhibitors, , antineoplastic agents, CC3 receptor antagonists, and antimicrobial agents. , Furthermore, QIs are precursors of their oxo-analogues, quinazolinones, which are known for their broad spectrum of therapeutic applications . In spite of their potential, only a few methods are available in the literature for the synthesis of QIs (Scheme ), and most of them have important limitations.…”

Section: Introductionmentioning

confidence: 99%

Polyphosphoric Acid Esters Promoted Synthesis of Quinazolin-4(3H)-imines from 2-Aminobenzonitrile

et al. 2023

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A novel method for the synthesis of quinazolin-4(3H)-imines (QIs) by trimethylsilyl polyphosphate (PPSE) promoted reaction of 2-aminobenzonitrile with secondary amides is reported. The reaction is general and allows for the synthesis of N 3 -aryl and N 3 -alkyl QIs with variable 2-substituents affording high yields. The procedure was extended to derivatives bearing additional functional groups. The method is operationally simple, involves easily available starting materials and a mild dehydrating agent, with wide functional group tolerance. The reaction procedure proved to be suitable for scaling-up. A possible reaction path via an intermediate nitrilium ion is proposed on the basis of literature data and experimental observations.

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Synthesis of 4(3H)quinazolinimines with selective cytotoxic effect on human acute promyelocytic leukemia cells

Cited by 8 publications

References 32 publications

Harnessing polarisation transfer to indazole and imidazole through signal amplification by reversible exchange to improve their NMR detectability

Harnessing polarisation transfer to indazole and imidazole through signal amplification by reversible exchange to improve their NMR detectability

Synthesis of Substituted Quinazolin-4(3H)-imines From Aryldiazonium Salts, Nitriles and 2-Cyanoanilines via A Metal-Free Tandem Approach

Polyphosphoric Acid Esters Promoted Synthesis of Quinazolin-4(3H)-imines from 2-Aminobenzonitrile

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